Structure Database (LMSD)
Common Name
N-arachidonoyl GABA
Systematic Name
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-γ-aminobutyric acid
Synonyms
- EMA-21
- Elmiric acid
- NAGABA
LM ID
LMFA08020074
Formula
Exact Mass
Calculate m/z
389.292994
Sum Composition
Status
Curated
3D model of N-arachidonoyl GABA
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
Several different arachidonoyl amino acids, including N-Arachidonoyl-γ-aminobutyric acid (NAGABA), have been isolated and characterized from bovine brain. The glycine congener (NAGly) was further characterized and found to suppress formalin-induced pain in rats. NAGABA was also found to suppress normal responses to pain, but has not been fully characterized to date.1
This information has been provided by Cayman Chemical
References
1. Huang, S.M., Bisogno, T., Petros, T.J., et al. Identification of a new class of molecules, the arachidonyl amino acids, and characterization of one member that inhibits pain. J. Biol. Chem. 276(46), 42639-42644 (2001).
String Representations
InChiKey (Click to copy)
JKUDIEXTAYKJNX-DOFZRALJSA-N
InChi (Click to copy)
InChI=1S/C24H39NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-20-23(26)25-22-19-21-24(27)28/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-22H2,1H3,(H,25,26)(H,27,28)/b7-6-,10-9-,13-12-,16-15-
SMILES (Click to copy)
N(CCCC(O)=O)C(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC
Other Databases
CHEBI ID
PubChem CID
SwissLipids ID
Cayman ID
GuidePharm ID
Calculated Physicochemical Properties
Heavy Atoms
28
Rings
0
Aromatic Rings
0
Rotatable Bonds
18
Van der Waals Molecular Volume
445.29
Topological Polar Surface Area
66.40
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
3
logP
6.40
Molar Refractivity
118.77
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Updated at
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